3-Methylsulfinyl-2-phenyl-1-benzofuran

The title compound, C15H12O2S, was prepared by the oxidation of 3-methylsulfanyl-2-phenyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 37.65 (8)° with the plane of the benzofuran fragment. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by aromatic π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.549 (2) Å] and by intermolecular C—H⋯O interactions.

The title compound, C 15 H 12 O 2 S, was prepared by the oxidation of 3-methylsulfanyl-2-phenyl-1-benzofuran with 3chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 37.65 (8) with the plane of the benzofuran fragment. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by aromaticinteractions between the benzene rings of neighbouring molecules [centroid-centroid distance = 3.549 (2) Å ] and by intermolecular C-HÁ Á ÁO interactions.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2109).
The benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9-C14) makes a dihedral angle of 37.65 (8)° with the plane of the benzofuran fragment. The molecular packing ( Fig. 2) is stabilized by aromatic π-π stacking interactions between the benzene rings from the adjacent molecules. The Cg···Cg ii distance is 3.549 (2) Å (Cg is the centroid of C2-C7 benzene ring, symmetry code as in Fig. 2). The crystal structure is further stabilized by C-H···O ( Fig. 2) interactions between a methyl H atom and the oxygen of the S=O unit, with a C15-H15C···O2 i separation of 2.36 Å ( Fig. 2 and Table 1; symmetry code as in Fig. 2).
Experimental 77% 3-Chloroperoxybenzoic acid (359 mg, 1.6 mmol) was added in small portions to a stirred solution of 3-methylsulfanyl-2-phenyl-1-benzofuran (360 mg, 1.5 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 2 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.95 Å for aromatic H atoms, 0.98 Å for methyl H atoms, respectively, and with U iso (H) = 1.2Ueq(C) for aromatic H atoms and 1.5Ueq(C) for methyl H atoms.